EP0794975B1 - Gegenstände mit dauerhaften farb- und/oder fluoreszenzeigenschaften - Google Patents
Gegenstände mit dauerhaften farb- und/oder fluoreszenzeigenschaften Download PDFInfo
- Publication number
- EP0794975B1 EP0794975B1 EP95936357A EP95936357A EP0794975B1 EP 0794975 B1 EP0794975 B1 EP 0794975B1 EP 95936357 A EP95936357 A EP 95936357A EP 95936357 A EP95936357 A EP 95936357A EP 0794975 B1 EP0794975 B1 EP 0794975B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- dye
- article
- hals
- fluorescent
- hindered amine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 230000001747 exhibiting effect Effects 0.000 title claims description 4
- 150000001412 amines Chemical class 0.000 claims description 39
- 229920000515 polycarbonate Polymers 0.000 claims description 36
- 239000004417 polycarbonate Substances 0.000 claims description 33
- 239000004611 light stabiliser Substances 0.000 claims description 31
- 239000011159 matrix material Substances 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 13
- -1 perylene imide Chemical class 0.000 claims description 12
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 9
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
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- 239000000975 dye Substances 0.000 description 68
- 239000003086 colorant Substances 0.000 description 21
- 239000007850 fluorescent dye Substances 0.000 description 18
- 238000011068 loading method Methods 0.000 description 18
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 17
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- SWZOQAGVRGQLDV-UHFFFAOYSA-N 4-[2-(4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yl)ethoxy]-4-oxobutanoic acid Chemical compound CC1(C)CC(O)CC(C)(C)N1CCOC(=O)CCC(O)=O SWZOQAGVRGQLDV-UHFFFAOYSA-N 0.000 description 2
- 229920013683 Celanese Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003522 acrylic cement Substances 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 230000002596 correlated effect Effects 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 238000004049 embossing Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- CBNSBRVOBGWOBM-UHFFFAOYSA-N 3-(5-chlorobenzoxazol-2-yl)-7-diethylaminocoumarin Chemical compound ClC1=CC=C2OC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 CBNSBRVOBGWOBM-UHFFFAOYSA-N 0.000 description 1
- STEYNUVPFMIUOY-UHFFFAOYSA-N 4-Hydroxy-1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CC(O)CC(C)(C)N1CCO STEYNUVPFMIUOY-UHFFFAOYSA-N 0.000 description 1
- UWSMKYBKUPAEJQ-UHFFFAOYSA-N 5-Chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2H-benzotriazole Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O UWSMKYBKUPAEJQ-UHFFFAOYSA-N 0.000 description 1
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 1
- 239000004716 Ethylene/acrylic acid copolymer Substances 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- 239000004418 Lexan Substances 0.000 description 1
- 229920005479 Lucite® Polymers 0.000 description 1
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- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
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- 230000005670 electromagnetic radiation Effects 0.000 description 1
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- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- PZRHRDRVRGEVNW-UHFFFAOYSA-N milrinone Chemical compound N1C(=O)C(C#N)=CC(C=2C=CN=CC=2)=C1C PZRHRDRVRGEVNW-UHFFFAOYSA-N 0.000 description 1
- 229960003574 milrinone Drugs 0.000 description 1
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- 238000007254 oxidation reaction Methods 0.000 description 1
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- 150000002978 peroxides Chemical class 0.000 description 1
- 238000007539 photo-oxidation reaction Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Images
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B44—DECORATIVE ARTS
- B44F—SPECIAL DESIGNS OR PICTURES
- B44F1/00—Designs or pictures characterised by special or unusual light effects
- B44F1/02—Designs or pictures characterised by special or unusual light effects produced by reflected light, e.g. matt surfaces, lustrous surfaces
- B44F1/04—Designs or pictures characterised by special or unusual light effects produced by reflected light, e.g. matt surfaces, lustrous surfaces after passage through surface layers, e.g. pictures with mirrors on the back
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/04—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof adapted as photovoltaic [PV] conversion devices
- H01L31/054—Optical elements directly associated or integrated with the PV cell, e.g. light-reflecting means or light-concentrating means
- H01L31/055—Optical elements directly associated or integrated with the PV cell, e.g. light-reflecting means or light-concentrating means where light is absorbed and re-emitted at a different wavelength by the optical element directly associated or integrated with the PV cell, e.g. by using luminescent material, fluorescent concentrators or up-conversion arrangements
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/52—PV systems with concentrators
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/25—Web or sheet containing structurally defined element or component and including a second component containing structurally defined particles
- Y10T428/252—Glass or ceramic [i.e., fired or glazed clay, cement, etc.] [porcelain, quartz, etc.]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31507—Of polycarbonate
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31536—Including interfacial reaction product of adjacent layers
Claims (10)
- Gegenstand mit dauerhaften Farb- und/oder Fluoreszenzeigenschaften, umfassend eine polymere Matrix, einen Farbstoff und einen sterisch gehinderten Amin-Lichtstabilisator, wobei der Farbstoff mindestens einen aus Thioxanthon, Perylenimid und Thioindigoid-Verbindungen ausgewählten Farbstoff enthält und die polymere Matrix Polycarbonat umfaßt.
- Gegenstand nach Anspruch 1, wobei der Gegenstand rückstrahlend ist.
- Gegenstand nach Anspruch 1, wobei der Gegenstand eine Folie ist.
- Gegenstand nach Anspruch 1, wobei der Gegenstand 0,01 bis 2,00 Gew.-% des Farbstoffs enthält.
- Gegenstand nach Anspruch 1, wobei der Gegenstand 0,10 bis 0,75 Gew.-% des sterisch gehinderten Amin-Lichtstabilisators enthält.
- Gegenstand nach Anspruch 1, wobei der sterisch gehinderte Amin-Lichtstabilisator eine 2,2,6,6-Tetramethylpiperidinverbindung umfaßt.
- Verfahren zur Herstellung eines Gegenstands mit dauerhaften Farb- und/oder Fluoreszenzeigenschaften, umfassend:
Extrudieren einer Polycarbonatmatrix, umfassend 0,01 bis 2,0 Gew.-% mindestens eines Farbstoffs, ausgewählt aus Thioxanthon, Perylenimid und Thioindigoid-Verbindungen, und 0,05 bis 1,00 Gew.-% eines sterisch gehinderten Amin-Lichtstabilisators. - Verfahren nach Anspruch 7, wobei der sterisch gehinderte Amin-Lichtstabilisator eine Verbindung aus der Klasse der 2,2,6,6-Tetramethylpiperidinverbindungen umfaßt.
- Verfahren zur Erhöhung der Beständigkeit von Polycarbonat, umfassend das Kombinieren des Polycarbonats mit einem sterisch gehinderten Amin-Lichtstabilisator und einem Farbstoff, wobei der Farbstoff mindestens einen aus Thioxanthon, Perylenimid und Thioindigoid-Verbindungen ausgewählten Farbstoff enthält.
- Verfahren nach Anspruch 9, wobei der sterisch gehinderte Amin-Lichtstabilisator eine 2,2,6,6-Tetramethylpiperidinverbindung ist.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US345608 | 1973-03-28 | ||
US34560894A | 1994-11-28 | 1994-11-28 | |
PCT/US1995/013340 WO1996017012A1 (en) | 1994-11-28 | 1995-10-11 | Articles exhibiting durable colour and/or fluorescent properties |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0794975A1 EP0794975A1 (de) | 1997-09-17 |
EP0794975B1 true EP0794975B1 (de) | 2000-02-09 |
Family
ID=23355714
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP95936357A Expired - Lifetime EP0794975B1 (de) | 1994-11-28 | 1995-10-11 | Gegenstände mit dauerhaften farb- und/oder fluoreszenzeigenschaften |
Country Status (9)
Country | Link |
---|---|
US (1) | US5605761A (de) |
EP (1) | EP0794975B1 (de) |
JP (1) | JP3447744B2 (de) |
KR (1) | KR100431164B1 (de) |
CN (1) | CN1071359C (de) |
AU (1) | AU700888B2 (de) |
CA (1) | CA2205805C (de) |
DE (1) | DE69515062T2 (de) |
WO (1) | WO1996017012A1 (de) |
Families Citing this family (89)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SG52631A1 (en) | 1990-01-22 | 1998-09-28 | Hoechst Roussel Pharma | Process for the enantioselection sznthesis of alkylated oxindoles used as intermediates in the preparation of physostigmine |
US5816238A (en) * | 1994-11-28 | 1998-10-06 | Minnesota Mining And Manufacturing Company | Durable fluorescent solar collectors |
JP4122057B2 (ja) | 1995-06-26 | 2008-07-23 | スリーエム カンパニー | 追加のコーティングまたは層を備えた多層ポリマーフィルム |
US6737154B2 (en) | 1995-06-26 | 2004-05-18 | 3M Innovative Properties Company | Multilayer polymer film with additional coatings or layers |
US6451408B1 (en) | 1995-06-29 | 2002-09-17 | 3M Innovative Properties Company | Retroreflective article |
AU6342596A (en) * | 1995-06-29 | 1997-01-30 | Minnesota Mining And Manufacturing Company | Wet retroreflective marking material |
US6703108B1 (en) | 1995-06-29 | 2004-03-09 | 3M Innovative Properties Company | Wet retroreflective marking material |
JPH11511592A (ja) * | 1995-08-28 | 1999-10-05 | ミネソタ マイニング アンド マニュファクチャリング カンパニー | 持続性のある蛍光ソーラコレクタ |
US5674622A (en) * | 1995-09-29 | 1997-10-07 | Minnesota Mining And Manufacturing Company | Fluorescent dye blends |
US5920429A (en) * | 1995-09-29 | 1999-07-06 | Minnesota Mining And Manufacturing Company | Fluorescent dye blends |
US6303058B1 (en) | 1996-06-27 | 2001-10-16 | 3M Innovative Properties Company | Method of making profiled retroreflective marking material |
US5783307A (en) * | 1996-11-04 | 1998-07-21 | Eastman Chemical Company | UV stabilized multi-layer structures with detectable UV protective layers and a method of detection |
AT409306B (de) * | 1997-10-03 | 2002-07-25 | Hoffmann La Roche | Optisch chemischer sensor |
US6110566A (en) * | 1997-10-23 | 2000-08-29 | 3M Innovative Properties Company | Stabilization of fluorescent dyes in vinyl articles using hindered amine light stabilizers |
US6001936A (en) | 1997-10-24 | 1999-12-14 | 3M Innovative Properties Company | Dye enhanced durability through controlled dye environment |
CA2306138A1 (en) * | 1997-10-31 | 1999-05-14 | Peter John Zanzucchi | Method for enhancing fluorescence |
US6191200B1 (en) | 1998-01-21 | 2001-02-20 | Reflexite Corporation | Extended life fluorescence polyvinyl chloride sheeting |
DE19839669C1 (de) * | 1998-09-01 | 2000-08-03 | Leo Baumann | Verfahren und Vorrichtung zur Simulation der Belastung von Materialien durch solare ultraviolette Strahlung |
GB9824314D0 (en) * | 1998-11-06 | 1998-12-30 | Clariant Int Ltd | New hetercyclic compounds |
WO2000047407A1 (en) * | 1999-02-12 | 2000-08-17 | Reflexite Corporation | Extended life fluorescence polyvinyl chloride sheeting |
US6472050B1 (en) | 1999-12-30 | 2002-10-29 | Avery Dennison Corporation | Light stable fluorescent vinyl suitable for use as a highway retroreflective roll-up sign |
US6958179B2 (en) * | 1999-12-30 | 2005-10-25 | 3M Innovative Properties Company | Segmented sheeting and methods of making and using same |
US6517664B1 (en) | 2000-01-10 | 2003-02-11 | Process Resources Corporation | Techniques for labeling of plastic, glass or metal containers or surfaces with polymeric labels |
US6533961B2 (en) * | 2000-02-22 | 2003-03-18 | 3M Innovative Properties Company | Durable fluorescent organic pigments and methods of making |
JP4028155B2 (ja) | 2000-04-11 | 2007-12-26 | 日本カーバイド工業株式会社 | 蛍光性再帰反射シート |
US6552787B1 (en) | 2000-09-29 | 2003-04-22 | General Electric Company | Rapid non-destructive screening methods for polymeric coatings and materials |
US6656319B1 (en) | 2000-10-25 | 2003-12-02 | 3M Innovative Properties Company | Fluid-activatable adhesive articles and methods |
US6972147B1 (en) | 2000-11-09 | 2005-12-06 | Avery Dennison Corporation | Fluorescent polymeric articles fabricated from U.V. light absorbing polymer |
US6514594B1 (en) | 2000-11-09 | 2003-02-04 | Avery Dennison Corporation | Fluorescent polymeric articles having screening layer formed from U.V. light absorbing polymer |
US6537679B1 (en) | 2000-11-09 | 2003-03-25 | Avery Dennison Corporation | Fluorescent articles of glycol-modified polyethylene terephthalate |
US6531205B1 (en) | 2001-02-14 | 2003-03-11 | Avery Dennison Corporation | Fluorescent yellow retroreflective sheeting |
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-
1995
- 1995-10-11 CN CN95196453A patent/CN1071359C/zh not_active Expired - Lifetime
- 1995-10-11 JP JP51876596A patent/JP3447744B2/ja not_active Expired - Lifetime
- 1995-10-11 CA CA002205805A patent/CA2205805C/en not_active Expired - Lifetime
- 1995-10-11 KR KR1019970703526A patent/KR100431164B1/ko not_active IP Right Cessation
- 1995-10-11 WO PCT/US1995/013340 patent/WO1996017012A1/en active IP Right Grant
- 1995-10-11 AU AU38341/95A patent/AU700888B2/en not_active Expired
- 1995-10-11 EP EP95936357A patent/EP0794975B1/de not_active Expired - Lifetime
- 1995-10-11 DE DE69515062T patent/DE69515062T2/de not_active Expired - Lifetime
-
1996
- 1996-05-21 US US08/650,964 patent/US5605761A/en not_active Expired - Lifetime
Also Published As
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---|---|
CA2205805A1 (en) | 1996-06-06 |
AU700888B2 (en) | 1999-01-14 |
JP3447744B2 (ja) | 2003-09-16 |
DE69515062D1 (de) | 2000-03-16 |
EP0794975A1 (de) | 1997-09-17 |
DE69515062T2 (de) | 2000-09-14 |
CN1168684A (zh) | 1997-12-24 |
CN1071359C (zh) | 2001-09-19 |
KR100431164B1 (ko) | 2004-09-16 |
MX9703689A (es) | 1997-10-31 |
AU3834195A (en) | 1996-06-19 |
JPH10510313A (ja) | 1998-10-06 |
US5605761A (en) | 1997-02-25 |
CA2205805C (en) | 2005-08-09 |
WO1996017012A1 (en) | 1996-06-06 |
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